Novel cationic amphiphiles with mannose-mimicking head-groups and a process for the preparation thereof
a technology of cationic amphiphiles and mannosemimicking head-groups, which is applied in the field of new cationic amphiphiles, can solve the problems of poor transfection efficiency of dendritic cells by liposomes prepared from cationic amphiphiles with mannosemimicking shikimic and quinic acid head-groups, insufficient immune response induced by naked dna topical injection, etc., and achieves enhanced cellular immune response respons
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example 1
[0081]Synthesis of the Cationic Amphiphile (1) (Scheme 1, X, n=13).
[0082]Step (i): Solid HOBt (0.28 g, 2 mmol) and EDCI (0.4 g, 2 mmol) were added sequentially to an ice cold and stirred solution of Nα—Z—Nε—BOC-L-Lysine (0.76 g, 2 mmol) in 5 mL dry DCM / dry DMF (9:1, v / v) under nitrogen atmosphere. After half an hour, N-2-aminoethyl-N,N-di-n-hexadecylamine (0.8 g, 1.5 mmol) dissolved in 5 mL dry DCM was added to the reaction mixture. The resulting solution was left stirred at 25° C. for 12 h, diluted with excess DCM and washed sequentially with saturated sodium bicarbonate (˜2×50 mL) and water (˜2×50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent from the filtrate removed by rotary evaporation. The residue upon column chromatographic purification with 60-120 mesh silica gel using 1-1.5% methanol in dichloromethane (v / v) as eluent afforded 1.1 g (80% yield) of the pure intermediate I. (Rf=0.5, 5% methanol in dichloromethane, v / v).
[0083]1H NMR ...
example 2
[0095]Synthesis of the Cationic Amphiphile (2) (Scheme 2, X, n=13)
[0096]Step (i): Solid HOBt (0.09 g, 0.67 mmol) and EDCI (0.13 g, 0.67 mmol) were added sequentially to an ice cold and stirred solution of 1,3,4,5-Tetraacetoxycyclohexane carboxylic acid (0.24 g, 0.67 mmol) in 5 mL dry DCM / dry DMF (9:1, v / v) under nitrogen atmosphere. After half an hour, the intermediate II as prepared in scheme 1 (0.38 g, 0.51 mmol) was dissolved in dry DCM was added to the reaction mixture. The resulting solution was left stirred at 25° C. for 12 h, diluted with excess DCM and washed sequentially with saturated sodium bicarbonate (˜3×50 mL) and water (˜3×50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent from the filtrate removed by rotary evaporation. The residue upon column chromatographic purification with 60-120 mesh silica gel using 1.5-2% methanol in dichloromethane (v / v) as eluent afforded 0.31 g (56% yield) of the pure intermediate I. (Rf=0.5, 5% meth...
example 3
Synthesis of Control Mannosylated Lipid (3) (Scheme 3):
[0106]Step (i): Solid HOBt (0.36 g, 2.3 mmol) and EDCI (0.45 g, 2.3 mmol) were added sequentially to an ice cold and stirred solution of 2-(tert-butyldiphenylsilyloxy)acetic acid (0.74 g, 2.3 mmol, a, scheme 3) in 5 mL dry DCM / thy DMF (9:1, v / v) under nitrogen atmosphere. After half an hour, intermediate N-2-[(Nε—Z-L-Lysyl)]aminoethyl-N,N-di-n-hexadecylamine (1.2 g, 1.5 mmol, prepared as described in Pramanik, D. et al. J Med Chem. 2008; 51:7298-7302) was dissolved in dry DCM was added to the reaction mixture. The resulting solution was left stirred at 25° C. for 12 h, diluted with excess chloroform and washed sequentially with saturated sodium bicarbonate (˜3×50 mL) and water (˜3×50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent from the filtrate removed by rotary evaporation. The residue upon column chromatographic purification with 60-120 mesh silica gel using 1-1.5% methanol in chlor...
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